Hydrochloric Acid → HCID 59543119, compound

HRID 1876347Notes

Reaction equation

HRID 1876347 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[C:9]([F:23])[CH:10]=[C:11]3[C:15]=2[NH:14][C:13]([C:16]2[S:17][CH2:18][C@@H:19]([CH2:21][OH:22])[N:20]=2)=[CH:12]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24]([O:26][C:27](=[O:30])[CH2:28]Br)[CH3:25].[H-].[Na+].Cl>O1CCCC1>[CH2:24]([O:26][C:27](=[O:30])[CH2:28][O:22][CH2:21][C@@H:19]1[CH2:18][S:17][C:16]([C:13]2[NH:14][C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([F:23])=[CH:8][C:7]=3[NH:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:20]1)[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 44126022HCID 44126022, compound

Product 1

HCID 59543119HCID 59543119, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (50 mg, 0.15 mmol) prepared in Example 5 was dissolved in tetrahydrofuran (5 ml). Bromoacetic acid ethyl ester (30 mg, 0.18 mmol) and sodium hydride (8 mg, 0.18 mmol) were added thereto, and the mixture was stirred for 3 h at room temperature. After completion of the reaction, 1N hydrochloric acid was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure, and purified by column chromatography to give the title compound (15 mg, Yield 24%) and the acid compound (40 mg, Yield 68%) of Example 171.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-b02bd3e09fb54a67891cf12308956435
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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